Dimethyl Sulfate → HCID 12665764, compound

HRID 267356Notes

Reaction equation

HRID 267356 reaction equation
[CH3:1][O:2][S:3]([O:6]C)(=[O:5])=[O:4].[CH3:8][N:9]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:10]1>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[CH3:1][N+:10]1[N:9]([CH3:8])[C:13]([Cl:14])=[CH:12][C:11]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 126657925-Chloro-1-methyl-3-phenyl-1H-pyrazole

Product 1

HCID 12665764HCID 12665764, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Dimethylsulfate (30 g, 0.22 mole) is added to a stirred solution of 1-methyl-5-chloro-3-phenylpyrazole (39.5 g, 0.2 mole) in dry xylene (350 ml) and the reaction mixture is warmed to 105°C to 115°C for 18 hours. A brown syrup separates out, the reaction is cooled and the xylene is decanted off. Dry acetone (300 ml) is added and after stirring a white precipitate separates out and is filtered off, m.p. 100°C to 102°C 33.8 g (55%). Recrystallization from dry acetone-toluene gives white needles m.p. 102°C to 104°C.

Workup

  1. temperaturethe reaction mixture is warmed to 105°C to 115°C for 18 hours
  2. temperaturethe reaction is cooled
  3. customthe xylene is decanted off
  4. additionDry acetone (300 ml) is added
  5. filtrationis filtered off
  6. customRecrystallization from dry acetone-toluene

Sources & evidence

ORD record
ord-37c3fad627b4441796870146eea3b13f
Source dataset
uspto-grants-1976_03
Patent number
US03941881

Reaction notes

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